One-Pot Synthesis of α,ω-Chain End Functional, Stereoregular, Star-Shaped Poly(lactide)

作者: Matthew J. Stanford , Andrew P. Dove

DOI: 10.1021/MA801977E

关键词:

摘要: The synthesis of stereoregular α,ω-chain end functional linear, telechelic, and star-shaped polymers copolymers is reported using a one-pot chain functionalization methodology. Aluminum methyl complexes are applied in combination with multifunctional initiating species to synthesize poly(lactide)s by the stereospecific ring-opening polymerization rac-lactide. quenching reactions an excess acid chloride molecules has enabled situ quantitative modification ω-chain ends such that primary secondary alkyl aryl groups can be incorporated. This methodology been extended “click” handles for both copper-catalyzed Huisgen 1,3-dipolar cycloaddition thiol−ene Michael additions block through application trithiocarbonate, suitable mediating RAFT polymerization. tolerant mild method used...

参考文章(51)
Koji Nakano, Naoyuki Kosaka, Tamejiro Hiyama, Kyoko Nozaki, Metal-catalyzed synthesis of stereoregular polyketones, polyesters, and polycarbonates Dalton Trans.. pp. 4039- 4050 ,(2003) , 10.1039/B304690G
Kenji Kurokawa, Koichi Yamashita, Yoshiharu Doi, Hideki Abe, Structural effects of terminal groups on nonenzymatic and enzymatic degradations of end-capped poly(L-lactide). Biomacromolecules. ,vol. 9, pp. 1071- 1078 ,(2008) , 10.1021/BM701259R
Christopher P. Radano, Gregory L. Baker, Milton R. Smith, Stereoselective polymerization of a racemic monomer with a racemic catalyst: Direct preparation of the polylactic acid stereocomplex from racemic lactide Journal of the American Chemical Society. ,vol. 122, pp. 1552- 1553 ,(2000) , 10.1021/JA9930519
Odile Dechy-Cabaret, Blanca Martin-Vaca, Didier Bourissou, Controlled ring-opening polymerization of lactide and glycolide. Chemical Reviews. ,vol. 104, pp. 6147- 6176 ,(2004) , 10.1021/CR040002S
Ashgan Bishara, Hans R Kricheldorf, Abraham J Domb, None, Stereocomplexes of Triblock Poly(lactide‐ PEG2000‐lactide) as Carrier of Drugs Macromolecular Symposia. ,vol. 225, pp. 17- 30 ,(2005) , 10.1002/MASY.200550703
Indra K. Varma, Ann-Christine Albertsson, Ritimoni Rajkhowa, Rajiv K. Srivastava, Enzyme catalyzed synthesis of polyesters Progress in Polymer Science. ,vol. 30, pp. 949- 981 ,(2005) , 10.1016/J.PROGPOLYMSCI.2005.06.010
Craig J. Hawker, Valery V. Fokin, M. G. Finn, K. Barry Sharpless, Bringing Efficiency to Materials Synthesis: The Philosophy of Click Chemistry Australian Journal of Chemistry. ,vol. 60, pp. 381- 383 ,(2007) , 10.1071/CH07107
Tina M. Ovitt, Geoffrey W. Coates, Stereochemistry of Lactide Polymerization with Chiral Catalysts: New Opportunities for Stereocontrol Using Polymer Exchange Mechanisms Journal of the American Chemical Society. ,vol. 124, pp. 1316- 1326 ,(2002) , 10.1021/JA012052+
Bryan Parrish, Rebecca B. Breitenkamp, Todd Emrick, PEG- and peptide-grafted aliphatic polyesters by click chemistry. Journal of the American Chemical Society. ,vol. 127, pp. 7404- 7410 ,(2005) , 10.1021/JA050310N
Hongzhi Du, Xuan Pang, Haiyang Yu, Xiuli Zhuang, Xuesi Chen, Dongmei Cui, Xianhong Wang, Xiabin Jing, Polymerization of rac-Lactide Using Schiff Base Aluminum Catalysts: Structure, Activity, and Stereoselectivity Macromolecules. ,vol. 40, pp. 1904- 1913 ,(2007) , 10.1021/MA062194U